Hydrochloric Acid → HCID 19855485, compound

HRID 1608063Notes

Reaction equation

HRID 1608063 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:8]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+].Cl>>[C:17]1([S:23]([NH:1][CH:2]2[CH2:11][CH2:10][C:9]3[C:8]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=[CH:5][C:4]=3[CH2:3]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14014982HCID 14014982, compound

Product 1

HCID 19855485HCID 19855485, compound

Procedure

10 mmol of 6-amino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetic acid and 20 mmol of benzenesulphonyl chloride are warmed at 80° C. in 40 ml of 10% strength NaOH for 2 hours. The mixture is then acidified with concentrated HCl and the milky suspension is extracted by shaking twice with ethyl acetate. The combined ethyl acetate phases are rapidly extracted by shaking with 10% strength NaOH (product precipitates out of the ethyl acetate), the NaOH phase is acidified with concentrated HCl and extracted by shaking twice with ethyl acetate and the extract is dried over Na2SO4 and evaporated. The residue is boiled up in ethyl acetate and the mixture is filtered. The product crystallizes out after 2-3 hours in a refrigerator.

Workup

  1. extractionthe milky suspension is extracted
  2. extractionThe combined ethyl acetate phases are rapidly extracted
  3. stirringby shaking with 10% strength NaOH (product
  4. customprecipitates out of the ethyl acetate), the NaOH phase
  5. extractionextracted
  6. stirringby shaking twice with ethyl acetate
  7. dry with materialthe extract is dried over Na2SO4
  8. customevaporated
  9. filtrationthe mixture is filtered
  10. customThe product crystallizes out after 2-3 hours in a refrigerator

Sources & evidence

ORD record
ord-d6852a01d7d64d30be532251d84b096c
Source dataset
uspto-grants-1989_09
Patent number
US04868331

Reaction notes

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